Sodium Hydroxide → HCID 58083444, compound

HRID 2404334Notes

Reaction equation

HRID 2404334 reaction equation
[OH-].[Na+].[CH2:3]([O:5][C:6]1[CH:11]=[C:10]([C:12]([O:14]C)=[O:13])[CH:9]=[CH:8][C:7]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]([F:25])([F:24])[F:23])[CH3:4]>CCO>[CH2:3]([O:5][C:6]1[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[CH:9]=[CH:8][C:7]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]([F:23])([F:24])[F:25])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58554210HCID 58554210, compound

Product 1

HCID 58083444HCID 58083444, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A 5 N aqueous solution of NaOH (4.1 mL, 20.5 mmol) was added into a solution of methyl 2-ethoxy-2′-(trifluoromethyl)biphenyl-4-carboxylate (4.45 g, 13.7 mmol) in EtOH (45 mL). The reaction mixture was heated at 60° C. for 30 minutes, and then concentrated under reduced pressure. The residue was taken up with water (50 mL) and a 5N aqueous solution of HCl (7 ml), and then extracted with MTBE (2×100 mL). The organic layers were washed with brine (50 mL), dried over MgSO4 and concentrated under reduced pressure to give a colorless oil. After precipitation from pentane, the title compound was obtained as a white powder. HPLC (Method A), Rt 4.3 min (purity: 99.7%). LC/MS (Method B): M− (ESI): 309.0.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractiona 5N aqueous solution of HCl (7 ml), and then extracted with MTBE (2×100 mL)
  3. washThe organic layers were washed with brine (50 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a colorless oil
  7. customAfter precipitation from pentane

Sources & evidence

ORD record
ord-7bbcd95ff1c54025be8bc7df758c7462
Source dataset
uspto-grants-2014_08
Patent number
US08802704B2

Reaction notes

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